Entire home

Waterfront dog-friendly Private Pier, Game Room at Jolly Roger

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Property grounds
Property grounds
Interior
Exterior
Terrace/patio

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 12223 sq m

Popular amenities

  • Barbecue grill
  • Washer
  • Outdoor space
  • Pet-friendly
  • Parking available
  • Air conditioning

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Waterfront dog-friendly Private Pier, Game Room at Jolly Roger

Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is open to guests and offers many water sporting opportunities during your stay! Nestled in the desirable quiet Arden on the Severn community. There are kids' and adult kayaks, canoes, stand-up paddle boards, fishing poles and crab traps. There are plenty of life jackets in the meticulous boat house. Sit on the back deck with unobstructed water views of the Severn River through the new glass railing. The deck has plenty of seating, a dining table and a gas grill.

Head inside the home to the living space on the main floor that stretches across the kitchen, family and dining rooms - all with MILLION DOLLAR WATER VIEWS. The Main Floor Master Bedroom has a King bed (split with individual controls), master bath with multiple shower heads, a bidet and a walk-in closet. There are two more guest rooms on the main floor with Queen beds that share a full bath in the hall.

The lower level is perfect for families with a large guest room with Queen Bed, a full bath and bunks for 4 kids or teens. Additional outdoor living space includes a large back yard, downstairs covered patio and a built-in firepit. The home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis.

SLEEPING ARRANGEMENTS 4 BR / 3 BA / Sleeps 8 adults and 4 kids/teens in bunks:
Main Floor Suite:
-King bed (Split with individual controls)
-Private Bathroom with Shower, bidet and vanity
-Large walk-in closet

Bedroom 1 on Main Floor:
-Queen bed
-Full Hall Bath

Bedroom 2 on Main Floor:
-Queen bed
-Full Hall Bath

Bedroom on lower level:
-Queen Bed
-Full Hall Bath

Bunk Room on lower level
-2 Bunks (4 Twin beds)
-Full Hall Bath

HIGHLIGHTS:
-Wrap-around deck with glass railing and water views a dining table and plenty of seating
-Water access from private pier on the Severn River
-BBQ Gas grill (propane tank provided)
-Spacious kitchen with stainless steel appliances
-Covered Patio on lower level
-Firepit
-Adult and kid kayaks (Life jackets provided)
-Lower level recreation room with foosball and indoor/outdoor ping pong table and TV
-Dining room table seats 10-12
-High Speed Internet and WiFi
-Smart Flatscreen TV's
-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
-Parking for multiple cars in driveway
-Full Laundry room with washer & dryer located inside the home
-Dogs allowed with $150 non-refundable fee paid prior to checkin

Property Distance to:
-Downtown Annapolis – 13 miles
-U.S. Naval Academy – 13 miles
-Washington, DC – 32 miles
-Baltimore - 25 miles

*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.
* All beds are made for you with freshly-laundered sheets & towels.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV
  • Video games

Outdoor areas

  • Balcony
  • Firepit
  • Garden
  • Gas grill
  • Outdoor furniture

Laundry

  • Laundromat nearby
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Foosball table
  • Kayak
  • Table tennis
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Garden
  • Unit size: 2,400 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

House
The Jolly Roger
Waterfront With Private Pier
New Waterfront Home With Private Pier Crownsville
New Waterfront Home With Private Pier Private vacation home
8301

About the area

Map
Crownsville, MD

What's nearby

  • Annapolis Mall Shopping Center - 16 min drive
  • Westfield Annapolis Mall - 16 min drive
  • Anne Arundel Medical Center - 17 min drive
  • Navy-Marine Corps Memorial Stadium - 20 min drive
  • U.S. Naval Academy - 21 min drive

Getting around

  • Odenton Station - 20 min drive
  • Baltimore Washington International Airport (BWI) - 32 min drive

Restaurants

  • ‪Chick-fil-A - ‬18 min drive
  • ‪McDonald's - ‬18 min drive
  • ‪Starbucks - ‬18 min drive
  • ‪Big Bean - ‬19 min drive
  • ‪Mi Pueblo II - ‬18 min drive

Frequently asked questions

Is Waterfront dog-friendly Private Pier, Game Room at Jolly Roger pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Waterfront dog-friendly Private Pier, Game Room at Jolly Roger?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront dog-friendly Private Pier, Game Room at Jolly Roger?

Checkout is at 11:00 AM.

Where is Waterfront dog-friendly Private Pier, Game Room at Jolly Roger located?

Located on the waterfront, this family-friendly holiday home is within 9 mi (15 km) of Joyces Marina, Annapolis Bowl and Annapolis Mall Shopping Center. Westfield Annapolis Mall and Eisenhower Golf Course are also within 9 miles (15 km).

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Waterfront dog-friendly Private Pier, Game Room at Jolly Roger Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 30 out of 31 reviews
Rating 8 - Good. 1 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Peter N.

Boatshow family gathering
Great house for the family to get together. Plenty of toys and things to do on the property. Sitting on the deck as the sun went down was a big hit.
Stayed 4 nights in Oct 2024

10/10 Excellent

Camilla M.

Perfect saty for family reunion
My nuclear family stayed here for a big family reunion weekend that was also in Crownsville. Absolutely perfect stay! Close to where we needed to be, plenty of space and activities for our downtime. Spent tons of time kayaking with all of the provided equipment, able to cook multiple meals and all implements were provided. Will definitely come back!
Stayed 3 nights in Aug 2024

10/10 Excellent

Linda H.

Fantastic View
This home has a beautiful deck, with a fantastic water view. The house has a well equipped kitchen, and updated bathrooms.
Stayed 3 nights in Jul 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jim C.

Family vacation
We had a great time at the Jolly Rogers on the Severn. I trip was great to work with. Very professional. Place was beautiful right on the water. Lots to do for all ages. Perfect location. Highly recommend
Stayed 3 nights in Jun 2024

10/10 Excellent

Helio M.

Great place
The house was amazing. The view is great, the place was really clean. The process was easy.
Stayed 3 nights in Mar 2024

10/10 Excellent

Nancy R.

Family Vacation
The house was well equipped and the views were amazing.
Stayed 3 nights in Sep 2023

10/10 Excellent

Joe H., St. Petersburg

Jolly Roger Vacation
We had a great experience staying at the Jolly Roger. The house was unique and was everything we had hoped for! I’m sure we’ll stay there again in the future!
Stayed 9 nights in Aug 2023

10/10 Excellent

Alyssa A.

Gorgeous views
Beautiful views, quiet location. Enjoyed watching the birds with our dog. Primary bedroom - comfortable large bed and very nice bathroom. Our son loved playing ping pong and foosball downstairs.
Stayed 2 nights in Mar 2024

10/10 Excellent

Treva G.

Great Family Getaway
We had a great time! It was wonderful to be able to prepare meals in the well appointed kitchen and play ping pong during the rainy times. We also enjoyed the deck and the dock. I would highly recommend this for a family getaway!
Stayed 3 nights in Jun 2023

10/10 Excellent

Garrett R.

Summer getaway
Great and very clean house with an outstanding deck over looking the Severn River
Stayed 3 nights in Jul 2023

10/10 Excellent

A.J. S.

Four couples long weekend
We had a really nice stay in Crownsville. We took the time to visit D.C. and Baltimore on the way home, brought the ferry over on the way. We all took advantage of what the house had to offer kayaking, fishing, a nice fire the one night and cards and games out on the deck each night. The house and that view couldn't have been better. The process didn't ask for too much on the way in or the way out and that's nice for the price. A fun getaway for all!!
Stayed 3 nights in May 2024

10/10 Excellent

Shankari S.

Pleasant stay
The pictures do not di justice to the besuty if the house and its location. The house has everything we needed for our big group of 10 people. Looking forward to staying here again.
Stayed 3 nights in Aug 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sarah W.

Spring break vacay
It was a beautiful home to be in with many activities for my children along with my two gfs children. There was plenty to do to entertain our children as it rained for a few days. The view was quite breathtaking and the host was very accommodating to our needs. We will def be back! Thanks!
Stayed 3 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kirra E.

Stay at the Jolly Roger
Home was so pretty and view was even better! We enjoyed the on-site paddle boards & kayaks. Girls trip was a success. Thank you!

10/10 Excellent

Walter G.

Nice Place Fantastic Sunset
House was very well equipped for all. Kids (toys) to adults (outdoor seating, dock , kayaks). Most definitely recommend for large gatherings
Stayed 2 nights in Nov 2023

10/10 Excellent

Suzanne H.

Wonderful location for a tough trip
Our family met in Maryland for a family funeral - and we booked the Jolly Roger, so we could all stay together. This place was FABULOUS - gorgeous views, plenty of room for us to be together and also have some alone time. We had some family visit with little kids and there were plenty of toys, a foosball table and ping pong table that kept them entertained. Truly, the house was the highlight of our trip. A number of people said they'd like to rent it again!
Stayed 4 nights in Mar 2024

10/10 Excellent

Maria B.

What a view
Wonderful home for a family gathering. We felt like we were staying with family as the house has a very lived in home feeling. We enjoyed all the activities offered but our favorite was sitting on the deck enjoying the view and each other's company.
Stayed 4 nights in Sep 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kimberly G.

Family getaway
House was nice and as-advertised. Beautiful view. Only thing to note are the many steps down to the dock which were not possible for an elderly parent, and the bunk beds are not in a room.
Stayed 6 nights in Jun 2023

10/10 Excellent

Verified traveller

What a beautiful view of the river!
Nice, comfortable place to stay with a large family group! Water views are beautiful. House had all the amenities you will need for a comfortable stay! Would like to stay during warm summer months to enjoy the water activities. Close to Baltimore, Annapolis and BWI.
Stayed 4 nights in Nov 2022

10/10 Excellent

Kevin G.

Jolly Roger
Great!
Stayed 6 nights in Jul 2023

10/10 Excellent

Betty M.

Amazing waterfront view !
Attended the Annapolis boat show. Location was a quick drive to downtown Annapolis House had everything you could ask for and more. Spectacular sunsets and a very quiet neighborhood. Would highly recommend. Just a beautiful home
Stayed 2 nights in Oct 2022

10/10 Excellent

Teresa S.

Family reunion
This property is great for extended families. The layout offers places to gather as well as options for alone time. The kitchen is extremely well stocked. High quality sheets and towels are provided. Young children are accommodated with high chairs and toys. Ping pong, foosball, kayaking, paddle boarding, canoeing, and fishing can keep guests entertained. Close (15ish minutes) to Annapolis and BWI.
Stayed 4 nights in Oct 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Crystal S.

The porch is to die for!
We spent 99% of our time on the back porch-we ate there, played there, and chatted. Great accommodations on the porch. The company was easy to work with and quick with communication. I would highly recommend renting a boat and keeping it at the dock. It was the highlight of the trip! Uber was not as accessible as we had hoped so I would rent a car if we visit again.

10/10 Excellent

Lucy A.

Set your sails for the Jolly Roger!
Nothing could beat the spectacular view! The Navy and nautical themes fit the setting -- and our family -- perfectly. I've never stayed in a house so well appointed -- every bowl, mug, dishware and kitchenware you could possibly want. An entire downstairs fitted out for kids (and kids at heart). Excellent location with good restaurants nearby and easy accesss to Annapolis. It made for a very memorable vacation for our adult family, even more special for us since we landed here after having to "salvage" our original vacation at the very last minute.
Stayed 3 nights in Aug 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rob W.

Great Family Rental
We just completed Thanksgiving at the Jolly Roger so we could spend the holiday with our Midshipman. We had 9 people at the house comfortably. The house is situated about halfway in between BWI and Annapolis - which is very convenient if you have folks flying in and out at different times. It sits beautifully on the Severn River. The morning views are fantastic. The house is clean and well-appointed. It is very roomy inside, so don't let the streetview concern you. We also found the management company proactive and responsive. This won't be our last time staying there.